HCID 18918306, compound → P-Toluenesulfonamide

HRID 1290473Notes

Reaction equation

HRID 1290473 reaction equation
C(C1C=CC(C[NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=CC=1)(=O)C>C(OCC)(=O)C>[CH3:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([NH2:11])(=[O:14])=[O:13])=[CH:20][CH:19]=1

Participants

3

Reactant 1

HCID 18918306HCID 18918306, compound

Product 1

HCID 6269P-Toluenesulfonamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product of step i) (1.0 g) and cupric bromide (1.47 g) in ethyl acetate (3.0 ml) was heated at reflux temperature for 16 hours. Additional cupric bromide (1.0 g) was added and heating continued for a further 8 hours. The mixture was filtered and the filtrate concentrated to dryness in vacuo. This residue was purified by flash chromatography on silica, eluting with hexane/ethyl acetate (2:1 v/v). Evaporation of the fractions gave N-(14-bromoacetylphenyl]methyl)-4-methylphenylsulphonamide, 1.13 g, as a white solid: m.p. 116°-117° C., NMR (CDl3) δ 7.9(2H,d), 7.75(2H,d), 7.34(4H,m), 4.77(1H,t), 4.40(2H,s), 4.22(2H,d), 2.44(3H,s): m/e 382/384 (M+H)+, 1 Br pattern.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 16 hours
  3. temperatureheating
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate concentrated to dryness in vacuo
  6. customThis residue was purified by flash chromatography on silica
  7. washeluting with hexane/ethyl acetate (2:1 v/v)
  8. customEvaporation of the fractions

Sources & evidence

ORD record
ord-ca186b1ddb5f4917b6e742dd36d80bb1
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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